Morpholine → HCID 19605509, compound

HRID 1603588Notes

Reaction equation

HRID 1603588 reaction equation
Br[C:2]1[CH:7]=[C:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[C:4]([Br:18])[N:3]=1.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C(N(CC)CC)C>O1CCOCC1>[Br:18][C:4]1[CH:5]=[C:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:7]=[C:2]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[N:3]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 110146744-(2,6-dibromopyridin-4-yl)sulfonylaniline

Product 1

HCID 19605509HCID 19605509, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

0.211 g (0.0005 mol) of 4-(2,6-dibromopyridine-4-sulphonyl)-phenylamine was dissolved in 10 ml of dioxane and treated with 0.217 g (0.0025 mol) of morpholine and 1 ml of triethylamine. The mixture was stirred at 40° C for 72 hrs. and the solvent was then removed. The residue was partitioned in ethyl acetate and water and the organic phase was extracted with sat. sodium chloride solution and dried over MgSO4. After removal of the solvent the residue was chromatographed on silica gel with ethyl acetate/hexane 1:1 and there was obtained 0.07 g (35%) of 4(2-bromo-6-morpholine-4-ylpyridine-4-sulphonyl)-phenylamine as white crystals; m.p.: 244-245° C.

Workup

  1. customand the solvent was then removed
  2. customThe residue was partitioned in ethyl acetate
  3. extractionwater and the organic phase was extracted with sat. sodium chloride solution
  4. dry with materialdried over MgSO4
  5. customAfter removal of the solvent the residue
  6. customwas chromatographed on silica gel with ethyl acetate/hexane 1:1

Sources & evidence

ORD record
ord-fc9623b1b9684df0958f3a4728e4a4ba
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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